The mentor mentioned in the email was Mike Volpi, then Cisco’s senior VP, who’s now an investor at Index Ventures.

But Bergelson never heard back from Volpi. Soon, he found out Volpi was leaving the company, and over the next four years at Cisco, Bergelson never had a mentor there.

Instead, Bergelson found a mentor outside of Cisco. That mentor — Yahoo chairman Maynard Webb — first reached out to Bergelson about a year before he left Cisco with a cold email, offering a job at LiveOps, the company he was running at the time. The offer never turned into a real job, but the two developed a strong mentor-mentee relationship since then.

In fact, that relationship is what inspired Bergelson to start his current startup Everwise. During his time at Cisco, Bergelson says he faced a lot of political battles, because he didn’t know much about corporate culture. Although he got promoted a few times and expanded his role there, Bergelson says he was never politically astute enough to think through some of things big companies value.

“If only I had someone like Maynard, I could have bounced some of these things off as I went through my time at Cisco,” Bergelson told Business Insider. “I would have done some things very differently.”

A two-way street

With Everwise, Bergelson wants to solve the mentorship problem many professionals face. And on Tuesday, Everwise announced that it’s raised a fresh Series A round of funding worth $8 million, led by Canvas Ventures, Sequoia Capital, and Webb Investment Network, to realise that goal.

Everwise’s software offers curated and personalised content that helps professional development, while matching people with mentors outside the company. The mentors are all voluntary and work with their mentees for at least 10 hours over a 6 month period. The curated content and mentors are provided using data analytics based on the user’s Linkedin profile and a separate personal assessment test, which includes a conversation with an individual manager who helps oversee the whole process.

“Learning experiences today in companies are very disparate. Our ambition is to tie all these things together into one platform that has the dataset about you and can give personalised experiences for you,” Bergelson said.

Bergelson says the mentorship program is a two-way learning experience. The mentees obviously benefit from learning from their mentors, but the mentors also like it because it gives them a chance to improve their coaching skills. Most of the mentors, now over a 1,000 registered, come from executive positions at Fortune 500 companies, spanning 130 different industries, with 91% of them coming back for another round of mentoring, Bergelson said.

Everwise claims to have over 100 customers now, including Twitter, Salesforce, and Oracle. It says 95% of the mentors are satisfied with their experience, while the companies that use its software are getting a year’s worth of training material at the same cost of a regular two-day training course. Bergelson wouldn’t disclose any sales figures, but said the company’s customer base has grown three-fold over the past year.

“It’s hard to find a mentor anywhere. It’s especially true when you’re at some of these big companies,” Bergelson said. “We’re focused on fixing mentorship and more broadly fixing talent development.”